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Exchange anywhere certificate error

i have configured my server as per the tutorial on this site to work with Outlook over HTTP.

i have configured outlook on an computer that is inside the LAN and it works perfectly.

when i configure my laptop which is outside the LAN i get an error saying there is a problem with the proxy server's security certificate. the security certificate is not from a trusted authority. outlook is unable to connect to the proxy server IP. (error code 38 ).

i have installed CA on the server and have installed the certificate into the trusted root certification authorities. (i am using vista on the laptop)

when i use OWA, i get a certificate error but can click through and OWA works perfectly.

Comment

Are you using a home grown certificate?
If so, I would suggest that you stop using a home grown certificate and use a commercial certificate. That will make it a much easier feature to deploy. When you can get SSL certificates for US$20/year it doesn't make any sense to try and use home grown certificates.

However it is important that you post what version of Exchange you are using. There is no such thing as "Exchange Anywhere". There is Outlook Anywhere which is Exchange 2007's version, Outlook over the Internet which is SBS 2003 and RPC over HTTPS which is Exchange 2003.
If you are using Exchange 2007 then the question not only needs to be moved, but the advice for certificates needs to be given with care.